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Synthesis 2000; 2000(9): 1241-1246
DOI: 10.1055/s-2000-6413
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6-O-Glycosylation of Morphine Derivatives Using Thioglycosides as Glycosyl Donors

Igor Rukhman, Lev Yudovich, Gennadiy Nisnevich, Arie L. Gutman
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Publication Date:
31 December 2000 (online)

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A novel approach was developed for the synthesis of the pharmaceutically important morphine and dihydromorphine 6-β-d-glucuronides. The key step involves a selective 6-O-glycosylation of 3-O-protected morphines and dihydromorphines with thioglycosides that serve as glycosyl donors in the presence of thiophilic promoters. This novel approach may be useful for the O-glycosylation of other alkaloid derivatives.

alkaloid glycosides - glycosylation - thioglycosides - morphine 6-β-d-glucuronide - dihydromorphine 6-β-d-glucuronide

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